Jenner, 65, who is using her recognition to help the trans community, is shown discussing some of the challenges trans people face.
"What's the big issue," Jenner asks her new girlfriends as they take a road trip.
"They're homeless and unemployed, so it's just going to take a lot more," says one.
Another woman suggests focusing on entry-level jobs "so that these girls have some alternative if they wanted," comments another.
And that's when Jenner's conservative views lead to some raised eyebrows.
"Don't a lot of times they can make more not working with social programs than they actually can with an entry-level job," she says. "You don't want people to get totally dependent on it. That's when they get in trouble – 'Why should I work? I got a few bucks, I got my room paid for.' "
Caitlyn Inc.: The Business of Jenner's New Life
Another woman says to camera that she's worried that Jenner's life "in the bubble" is an impediment to understanding other people's problems.
"Caitlyn has every right to be just as conservative as she choses, but many transgender men and women need social programs to survive, and that's nothing to be ashamed of," she says. "If Cait's going to be a spokesperson for the community. This is something she's going to have to understand."
I Am Cait airs Sundays at 8 p.m. ET on E!